KR101731366B1 - Composite plasticizer composition, and method for preparing the same, and polymer resin composition using the same - Google Patents
Composite plasticizer composition, and method for preparing the same, and polymer resin composition using the same Download PDFInfo
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- KR101731366B1 KR101731366B1 KR1020160119912A KR20160119912A KR101731366B1 KR 101731366 B1 KR101731366 B1 KR 101731366B1 KR 1020160119912 A KR1020160119912 A KR 1020160119912A KR 20160119912 A KR20160119912 A KR 20160119912A KR 101731366 B1 KR101731366 B1 KR 101731366B1
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0066—Flame-proofing or flame-retarding additives
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L27/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers
- C08L27/02—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L27/04—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment containing chlorine atoms
- C08L27/06—Homopolymers or copolymers of vinyl chloride
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L55/00—Compositions of homopolymers or copolymers, obtained by polymerisation reactions only involving carbon-to-carbon unsaturated bonds, not provided for in groups C08L23/00 - C08L53/00
- C08L55/02—ABS [Acrylonitrile-Butadiene-Styrene] polymers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
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- Compositions Of Macromolecular Compounds (AREA)
Abstract
The present invention relates to a composite plasticizer composition comprising a terephthalate derivative mixture and a dialkyl phthalate compound, a process for producing the same, and a polymer resin composition containing the same, and by using the composite plasticizer composition according to the present invention, A polymer resin composition excellent in physical properties such as 100% modulus, elongation percentage, and volatilization loss.
Description
The present invention relates to a composite plasticizer composition, a method for producing the same, and a polymer resin composition using the same.
Polymer resins are used in a variety of fields such as household goods, home appliances, clothing, automobiles, construction materials, and packaging materials depending on their characteristics. Polyethylene (PE), polypropylene (PP), polystyrene (PP), polyurethane (PU) and polyvinyl chloride (PVC) are widely used.
In particular, PVC resin is applicable to various applications ranging from household goods to industrial materials because it has hardness, softness characteristics and various molding ability and is excellent in price competitiveness and has universal utility. Such a PVC resin is not used alone, and a plasticizer is added for various properties.
Plasticizers provide flexibility to PVC resins and improve processability and compatibility. However, as the industry has developed, plasticizers have become more flexible not only in flexibility, but also in properties required for their applications, such as resistance to aging, cold resistance, oil resistance, water resistance, resistance to heat and heat.
Generally, the larger the molecular weight of the plasticizer, the better the aging resistance, but the compatibility with the vinyl chloride resin tends to be lowered. Accordingly, plasticizers suitable for aging and compatibility are selected according to application fields. In addition, plasticizers satisfying environmental regulations are excellent in room temperature and aging properties, but have a problem of deteriorating workability.
For example, diisodecyl phthalate (DIDP, Diisodecyl phthalate), which has been conventionally used as a plasticizer for a polymer resin such as a polyvinyl chloride resin, is highly environmentally harmful although it can impart excellent properties to a polymer resin. (Korean Patent No. 10-2015-0042159).
Therefore, it is urgent to develop a new plasticizer that meets the requirements of the physical properties and usage of the plasticizer in accordance with such environmental regulations.
In order to solve the above problems, the present invention provides an environmentally friendly plasticizer which is harmless to the human body and is mixed with a polymer resin to provide a polymer resin composition having excellent physical properties such as tensile strength, elongation, 100% modulus, elongation percentage, .
In order to accomplish the above object, the present invention provides a process for preparing a compound represented by the following general formula (1), comprising 1 to 20% by weight of a compound of the formula (1), 1 to 30% 1 to 70% by weight of a compound of the following formula (5), and 1 to 80% by weight of a compound of the following formula (6); And a phthalate compound represented by the following general formula (7), wherein the weight ratio of the terephthalate derivative mixture: phthalate compound is 5 to 95: 95 to 5.
[Chemical Formula 1]
(2)
(3)
[Chemical Formula 4]
[Chemical Formula 5]
[Chemical Formula 6]
(7)
Another aspect of the present invention relates to a polymer resin composition comprising the composite plasticizer composition.
Another aspect of the present invention relates to a molded article comprising the polymeric resin composition.
Another embodiment of the present invention is a process for preparing a terephthalate derivative mixture by reacting a reaction solution comprising 2-ethyl-1-hexanol, isononyl alcohol, 2-propyl-1-heptyl alcohol and terephthalic acid step; And b) mixing the synthesized terephthalate derivative mixture with a phthalate compound of the following formula (VII).
(7)
The composite plasticizer composition according to the present invention is an environmentally friendly plasticizer harmless to the human body and can provide a polymer resin composition having excellent compatibility and improved physical properties such as processability, heat loss, heat resistance, aging resistance and weather resistance when used in a polymer resin have.
Hereinafter, the composite plasticizer composition according to the present invention, the method for producing the same, and the polymer resin composition using the composite plasticizer composition will be described in detail.
It will be apparent to those skilled in the art that the technical and scientific terms used herein may have other meanings as commonly understood by one of ordinary skill in the art to which the present invention belongs. Descriptions of the blurred notice function and configuration are omitted.
The present inventors have found that although diisodecyl phthalate (DIDP, Diisodecyl phthalate), which has heretofore been used as a plasticizer for a polymer resin such as a polyvinyl chloride resin, can give excellent properties to a polymer resin, it has a high environmental hazard, (2-propylheptyl) phthalate, which is a mixture of terephthalate derivative and di (2-propylheptyl) phthalate, is an environmentally friendly plasticizer harmless to human body, And thus the present invention has been completed.
That is, the present invention relates to a composite plasticizer composition comprising a mixture of a terephthalate derivative and di (2-propylheptyl) phthalate, which provides an environmentally friendly plasticizer which is harmless to the human body and which is mixed with a polymer resin, , 100% modulus, elongation percentage, volatilization loss and the like.
In detail, the composite plasticizer composition according to an embodiment of the present invention comprises 1 to 20% by weight of a compound of the following formula 1, 1 to 30% by weight of a compound of the following formula 2, 1 to 50% by weight of a compound of the following formula 3, 1 to 30% by weight of a compound of the formula (5), 1 to 70% by weight of a compound of the formula (5), and 1 to 80% by weight of a compound of the formula (6); And a phthalate compound represented by the following formula (7), wherein the weight ratio of the terephthalate derivative mixture: phthalate compound may be 5 to 95: 95 to 5.
[Chemical Formula 1]
(2)
(3)
[Chemical Formula 4]
[Chemical Formula 5]
[Chemical Formula 6]
(7)
The composite plasticizer composition in which the terephthalate derivative mixture and the di (2-propylheptyl) phthalate are mixed at a specific ratio is an environmentally friendly plasticizer that is harmless to the human body. The plasticizer is excellent in compatibility, It is possible to provide a polymer resin composition improved in physical properties such as weight loss, heat resistance, aging resistance and weather resistance. On the other hand, when the compound of the formula (1) or the compound of the formula (6) is used singly, physical properties such as heat resistance and aging resistance may be poor. When the weight percentage is out of the range, tensile strength, elongation, 100% modulus, Or physical properties such as volatilization loss may be reduced.
More preferably, the composite plasticizer composition according to an embodiment of the present invention comprises 1 to 10% by weight of the compound of formula 1, 5 to 15% by weight of the compound of formula 2, 10 to 40% by weight of the compound of formula 3, To 15% by weight, the compound of formula (5): 10 to 30% by weight, and the compound of formula (6): 10 to 40% by weight; And a phthalate compound represented by the following formula (7), wherein the weight ratio of the terephthalate derivative mixture: phthalate compound may be 20-40: 80-60.
By satisfying the above range, it is possible to give the polymer resin similar or better mechanical properties and aging properties to DIDP as a commercial plasticizer when used in a polymer resin. Specifically, it has excellent tensile strength of 1.5 to 2.0 kfg / mm 2, elongation of 360 to 380%, 100% modulus of 0.58 to 0.65 kfg / mm 2, elongation percentage of 78 to 90%, and loss of volatilization of 0 to 7% It may have physical properties, and the phenomenon of bleeding may not occur. At this time, each physical property may be measured according to a measuring method to be described later.
The process for preparing such a composite plasticizer composition comprises the steps of: a) reacting a reaction solution containing 2-ethyl-1-hexanol, isononyl alcohol, 2-propyl-1-heptyl alcohol and terephthalic acid to synthesize a terephthalate derivative mixture step; And b) mixing the synthesized terephthalate derivative mixture with a phthalate compound represented by the following formula (7).
(7)
Specifically, in step a) according to an embodiment of the present invention, 0.2 to 0.5 mol of 2-ethyl-1-hexanol, 0.4 to 0.8 mol of isononyl alcohol, 2-propyl-1 And 0.8 to 1.2 moles of heptyl alcohol. 1 to 20% by weight of the compound of the formula 1, 1 to 30% by weight of the compound of the formula 2, 1 to 50% by weight of the compound of the formula 3, 1 to 30% by weight of the compound of the formula 4, 1 to 70% by weight of the compound of the formula (5), and 1 to 80% by weight of the compound of the formula (6) can be synthesized.
In this case, the reaction may be carried out at 230 to 250 ° C for 10 to 20 hours in step a). The esterification reaction can be effectively carried out under such reaction conditions, and the compounds of the formulas (1) to (6) can be synthesized within the above range.
In one embodiment of the present invention, step b) is a step of mixing the synthesized terephthalate derivative mixture with a phthalate compound of formula (7), i.e. di (2-propylheptyl) phthalate, wherein the weight ratio of terephthalate derivative mixture: 5 to 95: 95 to 5. It is possible to provide a polymer resin composition which is excellent in compatibility in such a range and has improved physical properties such as processability, heat loss, heat resistance, aging resistance and weather resistance when mixed with a polymer resin.
More preferably, the weight ratio of the terephthalate derivative mixture: phthalate compound may be 20-40: 80-60. When the above range is satisfied, a tensile strength of 1.5 to 2.0 kfg / mm 2, an elongation of 360 to 380%, a 100% modulus of 0.58 to 0.65 kfg / mm 2, an elongation percentage of 78 to 90%, a volatilization loss of 0 to 7% And the bridging phenomenon may not occur.
Also, as mentioned above, the composite plasticizer composition according to the present invention can be applied to a polymer resin. That is, the present invention can provide a polymer resin composition comprising a composite plasticizer composition.
In one embodiment of the present invention, the polymer resin may include, but is not limited to, a polyvinyl chloride resin, an olefin resin, an ABS resin, an acrylic resin, a polyester resin, ) Resin. By applying the composite plasticizer composition according to the present invention to the polyvinyl chloride resin, the physical properties such as tensile strength, elongation, 100% modulus, elongation percentage and volatilization loss can be maximized.
In one embodiment of the present invention, the composite plasticizer composition may be added in an amount of 20 to 120 parts by weight, more preferably 30 to 100 parts by weight, and more preferably 40 to 90 parts by weight, based on 100 parts by weight of the polymer resin . In such a range, physical properties such as tensile strength, elongation, 100% modulus, elongation percentage, and volatilization loss can be improved. In particular, when polyvinyl chloride resin is used as the polymer resin, A tensile strength in the range of 60 to 60%, a stretch ratio of 360 to 380%, a 100% modulus of 0.58 to 0.65 kfg / mm 2, an elongation percentage of 78 to 90%, and a volatilization loss of 0 to 7% May not occur.
The polymer resin composition may further include one or more additives selected from secondary plasticizers, stabilizers, fillers, lubricants, flame retardants, viscosity regulators, foaming agents, enhancers, pigments and the like. The additive is not particularly limited, but may be added in an amount of 0.1 to 10 parts by weight, more preferably 1 to 5 parts by weight, based on 100 parts by weight of the polymer resin. Within this range, each additive can achieve the desired effect.
Further, the present invention can provide a molded article produced from the above-described polymer resin composition. Specifically, the molded article may be used in various applications such as silver wallpaper, compound, wire compound, sheet, film, tarpaulin, hose, shoe, sealant, office supplies, gloves, bottle cap, Flooring materials, electromechanical parts, and the like.
Hereinafter, the composite plasticizer composition according to the present invention, the method for producing the same, and the polymer resin composition containing the same will be described in more detail with reference to examples. It should be understood, however, that the invention is not limited to the disclosed embodiments, but, on the contrary, is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the invention.
Unless otherwise defined, all technical and scientific terms have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. In addition, the unit of the additives not specifically described in the specification may be% by weight.
First, the physical properties of the prepared specimens were measured by the following method.
1) Tensile strength (kfg / ㎟): The test was carried out in accordance with KS M 3156.
2) Elongation (%): The test was carried out in accordance with KS M 3156.
3) 100% modulus (kfg / ㎟): Tensile strength at 100% elongation of test specimen by tensile, which means plasticization efficiency, and lower 100% modulus value indicates superior plasticization efficiency of material do.
4) Elongation percentage (%): The test piece was left in a Geer Oven at 113 ° C for 168 hours under aging conditions, and then calculated as (elongation of test piece after aging / elongation of test piece before aging) × 100. The closer this value is to 100%, the similar mechanical properties as before aging are exhibited. This property means the durability of wire compound can be maintained and used for a long time. The tensile strength of the specimens was measured in accordance with KS M 3156.
5) Volatilization loss (% by weight): The test piece was left in a Geer Oven at 113 ° C for 168 hours under aging conditions and then calculated as (weight of test piece after aging / weight of test piece before aging) × 100.
[Example 1]
158 g of 2-ethyl-1-hexanol, 263 g of isononyl alcohol, 481 g of 2-propyl-1-heptyl alcohol and 389 g of terephthalic acid were subjected to esterification at 240 DEG C for 18 hours.
After the completion of the reaction, the mixture was purified to obtain a terephthalate derivative mixture in which the compounds of the following general formulas (1) to (6) were mixed.
[Chemical Formula 1]
(2)
(3)
[Chemical Formula 4]
[Chemical Formula 5]
[Chemical Formula 6]
The resultant terephthalate derivative mixture was analyzed by a GC-Mass analyzer. As a result, it was found that the weight percentage of the terephthalate derivative mixture was 5:10: 30: 10: 15: 30.
Next, 70 parts by weight of di (2-propylheptyl) phthalate (DPHP, di (2-propylheptyl) phthalate) was added to 30 parts by weight of the obtained terephthalate derivative mixture to prepare a composite plasticizer composition.
[Example 2]
Weight percent of each compound in the terephthalate derivative mixture by varying the amount of the alcohol compound to be added is in the range of from 8: 12: 28: 10: 15: 27 as the weight% of the compound of Formula (6) All the steps other than the above were carried out in the same manner as in Example 1.
[Example 3]
Weight ratio of each compound in the terephthalate derivative mixture by varying the amount of the alcohol compound added is 12: 18: 35: 9: 21: 5 by weight in the formula (1) All the steps other than the above were carried out in the same manner as in Example 1.
[Example 4]
Except that 75 parts by weight of di (2-propylheptyl) phthalate was added to 25 parts by weight of the terephthalate derivative mixture to prepare a composite plasticizer composition.
[Example 5]
Except that 85 parts by weight of di (2-propylheptyl) phthalate was mixed with 15 parts by weight of a terephthalate derivative mixture to prepare a composite plasticizer composition.
[Comparative Example 1]
Weight percent of each compound in the terephthalate derivative mixture by varying the amount of the alcohol compound to be added is in the range of 30: 5: 10: 30: 10: 15 by weight in the composition of Formula 1: Formula 3: Formula 4: All the steps other than the above were carried out in the same manner as in Example 1.
[Comparative Example 2]
Except that 2-ethyl-1-hexanol and isononyl alcohol were used as the alcohol compound, the procedure of Example 1 was repeated to obtain the weight of the compound of Formula 1: Formula 3: Formula 4: Formula 5: % Of 30: 40: 0: 30: 0: 0.
[Comparative Example 3]
Except that isononyl alcohol and 2-propyl-1-heptyl alcohol were used as the alcohol compound, the procedure of Example 1 was repeated to obtain the weight of the compound of Formula 1: Formula 3: Formula 4: Formula 5: % Is 0: 30: 40: 0: 0: 30.
[Comparative Example 4]
Except that 2-ethyl-1-hexanol and 2-propyl-1-heptyl alcohol were used as an alcohol compound, the procedure of Example 1 was repeated to obtain a compound represented by Formula 1: Formula 2: Formula 4: : A terephthalate derivative mixture having a weight percentage of the formula (6) of 30: 0: 40: 0: 30: 0 was prepared.
[Comparative Example 5]
Except that 95 parts by weight of di (2-propylheptyl) phthalate was mixed with 5 parts by weight of a terephthalate derivative mixture to prepare a composite plasticizer composition.
[Comparative Example 6]
Except that 20 parts by weight of di (2-propylheptyl) phthalate was mixed with 80 parts by weight of a terephthalate derivative mixture to prepare a composite plasticizer composition.
(Parts by weight)
[ Manufacturing example 1 to 5, and Comparative Manufacturing Example 1-6]
70 parts by weight of the composite plasticizer composition prepared in Examples 1 to 5 and Comparative Examples 1 to 6 and 100 parts by weight of a stabilizer (CZ-400, manufactured by Dainippon Ink and Chemicals, Inc.) were added to 100 parts by weight of a polyvinyl chloride resin (PVC resin, Complex of Ca-Zn organics, Songwon Industrial Co., Ltd.) were added, and the mixture was kneaded at 165 ° C for 5 minutes using a Two-Roll Mill. Thereafter, a pressure of 15 MPa was applied at 175 캜 for 3 minutes using a heating press, and after cooling to 90 캜 or lower, a specimen was prepared. The properties of the specimens were measured and the values are shown in Table 2 below.
[ Comparative Manufacturing Example 7]
Except that diisodecyl phthalate (DIDP) was used as a plasticizer, and the physical properties of the specimens were measured. The values are shown in Table 2 below.
(kfg / mm < 2 &
(%)
(kfg / mm < 2 &
(%)
(weight%)
As shown in Table 2, in Examples 1 to 5 using the terephthalate derivative mixture and DPHP according to the present invention in a specific ratio as a plasticizer, similar or better physical properties were obtained as compared with the commercial plasticizer DIDP can confirm.
On the other hand, in Comparative Preparation Example 1 in which the weight percentage of each compound is out of the weight percentage range of the present invention in the terephthalate derivative mixture, it can be confirmed that the elongation percentage, elongation percentage and volatilization loss are reduced.
In addition, in Comparative Production Examples 2 to 4 using only two kinds of alcohol compounds, unlike the present invention, it can be confirmed that elongation percentage, elongation percentage and volatilization loss are lowered or bleeding phenomenon occurs.
Further, in Comparative Production Examples 5 and 6 in which the weight ratio of DPHP was out of the range of the present invention, it was confirmed that the elongation percentage, the elongation percentage and the volatilization loss were lowered or the bleeding phenomenon occurred.
As described above, it was confirmed that the effects of using the compounds of the formulas (1) to (6) were excellent, and that the mixing ratio of the respective terephthalate derivative compounds and the mixing ratio of DPHP affect the performance of the composite plasticizer .
While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed exemplary embodiments, but, on the contrary, Various modifications and variations may be made thereto by those skilled in the art.
Accordingly, the spirit of the present invention should not be construed as being limited to the embodiments described, and all of the equivalents or equivalents of the claims, as well as the following claims, belong to the scope of the present invention .
Claims (7)
[Chemical Formula 1]
(2)
(3)
[Chemical Formula 4]
[Chemical Formula 5]
[Chemical Formula 6]
(7)
The composite plasticizer composition comprises
1 to 10% by weight of the compound of the formula 1, 5 to 15% by weight of the compound of the formula 2, 10 to 40% by weight of the compound of the formula 3, 5 to 15% by weight of the compound of the formula 4, 10 to 30% And 10 to 40% by weight of a compound of formula (VI); And a phthalate compound represented by the following general formula (7), wherein the weight ratio of the terephthalate derivative mixture: phthalate compound is 20-40: 80-60.
Wherein the composite plasticizer composition is added in an amount of 30 to 120 parts by weight based on 100 parts by weight of the polymer resin.
Wherein the polymer resin is any one or two or more selected from a polyvinyl chloride resin, an olefin resin, an ABS resin, an acrylic resin, and a polyester resin.
b) mixing the synthesized terephthalate derivative mixture with a phthalate compound of Formula 7;
≪ / RTI >
(7)
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| KR1020160119912A KR101731366B1 (en) | 2016-09-20 | 2016-09-20 | Composite plasticizer composition, and method for preparing the same, and polymer resin composition using the same |
| PCT/KR2017/010238 WO2018056666A1 (en) | 2016-09-20 | 2017-09-19 | Composite plasticizer composition, method for preparing same, and polymer resin composition using same |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2018056666A1 (en) * | 2016-09-20 | 2018-03-29 | 애경유화 주식회사 | Composite plasticizer composition, method for preparing same, and polymer resin composition using same |
| KR20190022286A (en) * | 2017-08-25 | 2019-03-06 | 애경유화주식회사 | Composite plasticizer composition, and method for preparing the same, and polymer resin composition using the same |
| WO2019039879A3 (en) * | 2017-08-25 | 2019-04-25 | 애경유화 주식회사 | Composite plasticizer composition, preparation method therefor, and polymer resin composition using same |
| KR20190110702A (en) * | 2018-03-21 | 2019-10-01 | 애경유화주식회사 | Composite plasticizer composition, and method for preparing the same, and polymer resin composition using the same |
| KR20220150063A (en) | 2021-05-03 | 2022-11-10 | (주)네오 | Novel dicyclohexyl ester composition and preparation thereof |
| KR20220150062A (en) | 2021-05-03 | 2022-11-10 | (주)네오 | Novel cyclohexane ester composition and preparation thereof |
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| DE102006001795A1 (en) * | 2006-01-12 | 2007-07-19 | Oxeno Olefinchemie Gmbh | Terephthalic acid dialkyl esters and their use |
| KR101570386B1 (en) * | 2012-10-25 | 2015-11-19 | 애경유화주식회사 | Composite plasticizer composition comprising epoxy ester compound and polymer resin composition using the same |
| KR101731366B1 (en) * | 2016-09-20 | 2017-04-28 | 애경유화주식회사 | Composite plasticizer composition, and method for preparing the same, and polymer resin composition using the same |
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- 2016-09-20 KR KR1020160119912A patent/KR101731366B1/en active IP Right Grant
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- 2017-09-19 WO PCT/KR2017/010238 patent/WO2018056666A1/en active Application Filing
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| JP2015083690A (en) | 2006-08-30 | 2015-04-30 | イーストマン ケミカル カンパニー | Terephthalates as plasticizers in vinyl acetate polymer compositions |
| KR101569560B1 (en) | 2012-10-10 | 2015-11-16 | 주식회사 엘지화학 | Plasticizer composition, method for preparing thereof, and heat-resistant resin composition |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018056666A1 (en) * | 2016-09-20 | 2018-03-29 | 애경유화 주식회사 | Composite plasticizer composition, method for preparing same, and polymer resin composition using same |
| KR20190022286A (en) * | 2017-08-25 | 2019-03-06 | 애경유화주식회사 | Composite plasticizer composition, and method for preparing the same, and polymer resin composition using the same |
| WO2019039879A3 (en) * | 2017-08-25 | 2019-04-25 | 애경유화 주식회사 | Composite plasticizer composition, preparation method therefor, and polymer resin composition using same |
| KR102108875B1 (en) * | 2017-08-25 | 2020-05-20 | 애경유화주식회사 | Composite plasticizer composition, and method for preparing the same, and polymer resin composition using the same |
| KR20190110702A (en) * | 2018-03-21 | 2019-10-01 | 애경유화주식회사 | Composite plasticizer composition, and method for preparing the same, and polymer resin composition using the same |
| KR102354744B1 (en) | 2018-03-21 | 2022-01-25 | 애경케미칼주식회사 | Composite plasticizer composition, and method for preparing the same, and polymer resin composition using the same |
| KR20220150063A (en) | 2021-05-03 | 2022-11-10 | (주)네오 | Novel dicyclohexyl ester composition and preparation thereof |
| KR20220150062A (en) | 2021-05-03 | 2022-11-10 | (주)네오 | Novel cyclohexane ester composition and preparation thereof |
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| Publication number | Publication date |
|---|---|
| WO2018056666A1 (en) | 2018-03-29 |
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